(7R,8R)-8-(benzyloxy)-7-(p-toluenesulfonyloxy)-2-methyloctadec-4-ene

Base Information

• Chemical Name: (7R,8R)-8-(benzyloxy)-7-(p-toluenesulfonyloxy)-2-methyloctadec-4-ene
• CAS No.: 936650-23-6
• Molecular Formula: C₃₃H₅₀O₄S
• Molecular Weight: 542.824
• Mol file: 936650-23-6.mol

Synonyms:(7R,8R)-8-(benzyloxy)-7-(p-toluenesulfonyloxy)-2-methyloctadec-4-ene

Chemical Property of (7R,8R)-8-(benzyloxy)-7-(p-toluenesulfonyloxy)-2-methyloctadec-4-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (7R,8R)-8-(benzyloxy)-7-(p-toluenesulfonyloxy)-2-methyloctadec-4-ene

There total 8 articles about (7R,8R)-8-(benzyloxy)-7-(p-toluenesulfonyloxy)-2-methyloctadec-4-ene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

(4R,5R)-5-(benzyloxy)-4-(p-toluenesulfonyloxy)pentadec-1-ene (936650-22-5) + 4-Methyl-1-pentene (691-37-2,25068-26-2) → (7R,8R)-8-(benzyloxy)-7-(p-toluenesulfonyloxy)-2-methyloctadec-4-ene (936650-23-6)

Guidance literature:

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; for 6h; Heating;

DOI:10.1021/jo070060o

Reference yield:

C41H66O4 → (7R,8R)-8-(benzyloxy)-7-(p-toluenesulfonyloxy)-2-methyloctadec-4-ene (936650-23-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 0.47 g / iron(III) chloride hexahydrate / CH₂Cl₂ / 2.5 h / 20 °C

2: lead(IV) acetate / benzene / 1.5 h / 20 °C

3: 0.18 g / magnesium bromide diethyl etherate / CH₂Cl₂ / 2 h / -78 °C

4: 87 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 5 h / 20 °C

5: 92 percent / Grubbs catalyst 2nd generation / CH₂Cl₂ / 6 h / Heating

With lead(IV) acetate; dmap; iron(III) chloride; magnesium bromide ethyl etherate; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; benzene; 3: Keck allylation;

DOI:10.1021/jo070060o

Reference yield:

(4R,5R)-4,5-diundecanoyl-2,2-dimethyl-1,3-dioxolane (936650-18-9) → (7R,8R)-8-(benzyloxy)-7-(p-toluenesulfonyloxy)-2-methyloctadec-4-ene (936650-23-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 93 percent / K-Selectride / tetrahydrofuran / 2.5 h / -78 °C

2: sodium hydride / dimethylformamide / 2 h / 0 °C

3: 0.47 g / iron(III) chloride hexahydrate / CH₂Cl₂ / 2.5 h / 20 °C

4: lead(IV) acetate / benzene / 1.5 h / 20 °C

5: 0.18 g / magnesium bromide diethyl etherate / CH₂Cl₂ / 2 h / -78 °C

6: 87 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 5 h / 20 °C

7: 92 percent / Grubbs catalyst 2nd generation / CH₂Cl₂ / 6 h / Heating

With lead(IV) acetate; dmap; iron(III) chloride; sodium hydride; potassium tri-sec-butyl-borohydride; magnesium bromide ethyl etherate; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; benzene; 5: Keck allylation;

DOI:10.1021/jo070060o

upstream raw materials:

(4R,5R)-5-(benzyloxy)-4-(p-toluenesulfonyloxy)pentadec-1-ene

4-Methyl-1-pentene

(4R,5R)-5-(benzyloxy)pentadec-1-en-4-ol

(4R,5R)-4,5-diundecanoyl-2,2-dimethyl-1,3-dioxolane